In his 1941 essay entitled “On Popular Music,” Theodor Adorno expresses serious doubt in the potential of popular music to transcend the strictures of hegemonic culture. Citing popular music’s all-encompassing “standardization” of form and content, Adorno sees in the rise of popular music the forward march of an all-encompassing mass culture. By upholding standardization as a preferable delineator between transformative and normative music to previous discourse centered on ideas of complexity, sophistication, or class, Adorno chooses to examine the popular as it applies to the individual. In this, he finds the popular guilty of providing a false sense of individuality while subtly ensuring the conformity of culture through recreational music. This dilemma is nowhere more clearly visible to Adorno than in the formulaic nature of popular tunes that can, with slight sonic modifications and requisite “plugging” from industry professionals, be forever replicated to commercial success. As the complicated legacy of “pop” from the 1960s onward demonstrates, Adorno’s wholesale dismissal of popular music fails however to anticipate its instrumental role in the formation of counter-cultural subjects in the post-war period. This blind spot is particularly curious; given Adorno’s acknowledgement of the presence of “bad ‘serious’ music,” one would expect him to at least offer the possibility of a suitably de-standardized form of popular music. As Adorno scholar Max Paddison notes in his volume, “Adorno, Modernism, and Mass Culture,” such a possibility can be read out of Adorno’s theory, even if he never explicitly acknowledges it. For Paddison, Adorno’s insistence upon standardization as inherent to popular music blinds him to its potential for subject formation. Thus, to conceive of a popular music discourse in which the popular’s revolutionary potential is acknowledged actually requires very little re-shuffling of Adorno’s original framework. As Paddison notes, The split is much more that between, on the one hand music which accepts its character as commodity, thus becoming identical with the machinations of the culture industry itself, and, on the other hand, a self-reflective music which critically opposes its fate as commodity, and thus ends up by alienating itself from society by becoming unacceptable to it. It is precisely this latter, subversive manifestation of popular – located in both musical and literary objects – with which this thesis is primarily concerned. Not only do I argue that popular art plays, contrary to the original Adornian view, a vital role in the formation of genuine subjectivity, I present evidence for the persistence of critical, political popular art in a time where many writers and scholars believe the popular to have forsaken countercultural possibilities once and for all. In building this case, I furthermore consider a unique phenomenon in twenty-first century German popular culture: the literary musician. While quite rare in the Anglosphere, musicians-turned-authors such as Schorsch Kamerun and Sven Regener, whose works I attend to in this thesis, constitute a hearty group in contemporary German literature. As we consider the dimensions of popular culture, it becomes clear that both music and literature are invested in thinking about the creation of political subjects and the problems of contemporary society. Kamerun’s and Regener’s literary texts approach these topics by remembering the dimensions of their own subject formation under the auspices of the state, delving into the Bildungsroman tradition to illuminate various possibilities for the development for a radicalized political consciousness. Turning to the music these authors make as young adults under the vastly different conditions present in unified Germany of the early 1990s, we see struggle to define the self replaced by a struggle to define communities of resistance to the institutions, politics, and morals of an increasingly immoral hegemonic culture. While their approaches and belief systems ultimately stand in conflict to one another, Kamerun’s and Regener’s literature and music reveal historically-rooted approaches to the twin political dilemmas of subjectivity and resistance amplified in turn by the Cold War’s reheating in the 1980s, and the fall of the Berlin Wall and the Neo-Nazi violence of Mölln and Rostock that christened the 1990s.